League Finals, held at Nikos Galis Olympic Indoor Hall, Olympiacos won in the game's second overtime period, after Spanoulis hit another game-winning 3 point field goal, with 1.9 seconds remaining in the game. He was subsequently named the 2016 Greek League MVP, and the 2016 Greek League Finals MVP. 2016–17 season In June 2016, Spanoulis signed a new 2-year contract extension with Olympiacos, lasting through the 2017–18 season. The contract was worth net income (€1.5 million net income per season). During that season's EuroLeague competition, Euroleague.net named Spanoulis the "Most Clutch Player in EuroLeague History". That same season, Spanoulis eventually led Olympiacos to the 2017 EuroLeague Final. 2017–18 season During the 2017–18 season, Spanoulis became the EuroLeague's all-time career leader in assists, and the Greek Professional Basket League's all-time career leader in points scored. He was also the 2018 Greek Cup Finals Top Scorer. In May 2018, he was named to the All-EuroLeague Second Team, of the 2017–18 season, the eighth All-EuroLeague Team selection of his career, which set a record for the most All-EuroLeague Team selections of all time. 2018–19 season Prior to the start of the 2018–19 season, Spanoulis signed a one-year contract extension with Olympiacos, on July 2, 2018, at a salary of €1.2 million net income. He was named the MVP of Round 14 of the 2018–19 EuroLeague season. During the Greek Basket League 2018–19 season, Spanoulis became the Professional Greek League's all-time career assists leader. He passed the previous record holder, Dimitris Diamantidis, in a Greek League game against AEK Athens, in January 2019. On 14 March 2019, Spanoulis suffered a season-ending peroneal tendon rupture on his right ankle, in a EuroLeague game against the Italian club Olimpia Milano. 2019–20 season After undergoing a 2018–19 season-ending right ankle surgery, for a peroneal tendon rupture, on 1 April 2019, Spanoulis began individual workouts again on 5 July 2019. After his return to individual training, Spanoulis signed a one-year contract extension with Olympiacos, at a salary of €600,000 net income. On 29 November 2019, Spanoulis passed Juan Carlos Navarro, to become the EuroLeague's all-time career leader in Performance Index Rating (PIR). He accomplished the milestone in a EuroLeague 2019–20 season game versus the Italian club Olimpia Milano. On 2 January 2020, Spanoulis also passed Navarro as the EuroLeague's all-time leading scorer since the 2000–01 season, in Olympiacos' loss against Fenerbahçe. On 4 February 2020, Spanoulis again suffered